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“What do you want me to wear?” I asked, knowing I only had a maintenance uniform or a prison jump suit.“The maintenance uniform and make sure to...keep your mouth shut about being incarcerated here.” she replied, looking at the tray I was handing back to her, “Do eat your pudding, desert is one of the only treats you will find here.”I pulled the tray back reluctantly, remembering the tainted batch I had the last time I ate it. Thinking that if it were such a treat, then aren’t I the lucky one. My tongue hungrily found its mark. Her mouth continued the rhythmic up and down movement on my shaft and the rain sounded like it might tear the vehicle apart. We were beyond caring, beyond everything. Suddenly, she dispelled the darkness with a guttural moan, “Uugggghhhhhhh,” followed by a shriek that startles me momentarily. She thrust and pushed her clit against my mouth, hard. Her thighs gripped the sides of my face, hard. Her body tensed and I realize she was cumming and cumming hard. It. When she asked what measures should be taken to ensure I get the point, I played on her choice of words. I think you should point the purple toy at my ass, honey. I held my breath as soon as the words left my lips. Over the past few years Jennifer had warmed up to anal sex quite nicely, finally allowing me to fully penetrate her ass, and even trying double penetration with the purple toy bent to accommodate both holes. Shes let me cum in her ass a few times since and she now craves my finger in. After an hour, I knew everything about her sexually from when she lost her virginity to all of her likes.I knew I had to fuck her but I didn't know how she would react to my advances. I made up a reason to go by her apartment that next Friday evening and when I got there, I moved some things around and played with her daughter. When her daughter went to sleep, I noticed Shana looked a little tense. I told her I had learned how to massage when I was in Japan and offered to give her a full body.
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